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Special Issue "Olefin Metathesis"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: closed (30 November 2015)

Special Issue Editor

Guest Editor
Dr. Georgios C. Vougioukalakis

Department of Chemistry, University of Athens, Panepistimiopolis, 15771 Athens, Greece
Website | E-Mail
Phone: +30-210-7274230
Interests: organic chemistry; coordination chemistry; organometallic chemistry; catalysis; materials chemistry; nanostructures; physical organic chemistry

Special Issue Information

Dear Colleagues,

Olefin metathesis is one of the most significant advancements of the last twenty years in the fields of organic chemistry, polymers synthesis, and materials science. It offers a new exciting toolbox of synthetic methods and, therefore, has conditioned the ways chemists design new molecules. Equally important, metathesis has stimulated the preparation of numerous fascinating novel compounds and materials in both industry and academia. The recognition of the great influence of olefin metathesis to the art of chemical synthesis led to the awarding of the 2005 Nobel Prize in Chemistry to Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock.

The goal of the present Special Issue of Molecules is to discuss recent developments in all fields of metathesis. The Special Issue welcomes submissions from all related research areas, including catalyst development, mechanistic and decomposition studies, substrate scope, polymers and materials synthesis, as well as applications in the synthesis of biologically-active compounds and theoretical calculations.

Dr. Georgios C. Vougioukalakis
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • catalyst development
  • mechanistic studies
  • olefin metathesis in organic synthesis
  • metathesis polymerizations
  • industrial applications
  • theoretical calculations

Published Papers (8 papers)

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Editorial

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Open AccessEditorial Recent Advances in Olefin Metathesis
Molecules 2016, 21(12), 1751; doi:10.3390/molecules21121751
Received: 19 December 2016 / Revised: 19 December 2016 / Accepted: 20 December 2016 / Published: 21 December 2016
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Abstract
Olefin metathesis is one of the most significant developments of the last 20 years in the fields of organic chemistry, polymers synthesis, and materials science [1–7]. [...]
Full article
(This article belongs to the Special Issue Olefin Metathesis)

Research

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Open AccessArticle Moving from Classical Ru-NHC to Neutral or Charged Rh-NHC Based Catalysts in Olefin Metathesis
Molecules 2016, 21(2), 177; doi:10.3390/molecules21020177
Received: 23 December 2015 / Revised: 13 January 2016 / Accepted: 28 January 2016 / Published: 30 January 2016
Cited by 5 | PDF Full-text (737 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Considering the versatility of oxidation states of rhodium together with the successful background of ruthenium-N-heterocyclic carbene based catalysts in olefin metathesis, it is envisaged the exchange of the ruthenium of the latter catalysts by rhodium, bearing an open-shell neutral rhodium center,
[...] Read more.
Considering the versatility of oxidation states of rhodium together with the successful background of ruthenium-N-heterocyclic carbene based catalysts in olefin metathesis, it is envisaged the exchange of the ruthenium of the latter catalysts by rhodium, bearing an open-shell neutral rhodium center, or a +1 charged one. In the framework of in silico experiments, density functional theory (DFT) calculations have been used to plot the first catalytic cycle that as a first step includes the release of the phosphine. DFT is, in this case, the tool that allows the discovery of the less endergonic reaction profile from the precatalytic species for the neutral catalyst with respect to the corresponding ruthenium one; increasing the endergonic character when dealing with the charged system. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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Open AccessArticle Exploring the Reactivity of Na[W2(μ-Cl)3Cl4(THF)2]∙(THF)3 towards the Polymerization of Selected Cycloolefins
Molecules 2015, 20(12), 21896-21908; doi:10.3390/molecules201219810
Received: 19 October 2015 / Revised: 24 November 2015 / Accepted: 30 November 2015 / Published: 8 December 2015
Cited by 5 | PDF Full-text (2310 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The bimetallic compound Na[W2(μ-Cl)3Cl4(THF)2]·(THF)3 (1, {W 3 W}6+, a′2e′4) is a highly efficient room-temperature initiator for ring opening metathesis polymerization (ROMP) of norbornene (NBE)
[...] Read more.
The bimetallic compound Na[W2(μ-Cl)3Cl4(THF)2]·(THF)3 (1, {W 3 W}6+, a′2e′4) is a highly efficient room-temperature initiator for ring opening metathesis polymerization (ROMP) of norbornene (NBE) and some of its derivatives. In most cases, addition of phenylacetylene (PA) as co-initiator improves the catalytic activity and retains the high cis-stereoselectivity. On the other hand, 1 can polymerize cyclopentadiene (CPD), not via a metathetic, but rather, via a cationic mechanism. Here, we present a comparison of the reactivity of the two catalytic systems (1 and 1/PA) between themselves and with other systems reported in the literature, the characterization of the polymers formed and mechanistic aspects of the corresponding reactions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
Figures

Open AccessArticle Olefin Metathesis Reaction in Water and in Air Improved by Supramolecular Additives
Molecules 2015, 20(10), 19130-19141; doi:10.3390/molecules201019130
Received: 23 September 2015 / Revised: 13 October 2015 / Accepted: 14 October 2015 / Published: 21 October 2015
Cited by 4 | PDF Full-text (1640 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by
[...] Read more.
A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by catalyst activation, improved mass transfer, and solubility of reactants in the aqueous reaction media. Additionally, the use of supramolecular additives allows lower catalyst loadings, but still high activity in pure water under aerobic conditions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
Figures

Open AccessArticle Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes
Molecules 2015, 20(9), 16892-16907; doi:10.3390/molecules200916892
Received: 17 August 2015 / Revised: 7 September 2015 / Accepted: 8 September 2015 / Published: 16 September 2015
Cited by 2 | PDF Full-text (805 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a
[...] Read more.
2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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Open AccessArticle Statistical Ring Opening Metathesis Copolymerization of Norbornene and Cyclopentene by Grubbs’ 1st-Generation Catalyst
Molecules 2015, 20(9), 15597-15615; doi:10.3390/molecules200915597
Received: 26 June 2015 / Revised: 18 August 2015 / Accepted: 19 August 2015 / Published: 27 August 2015
Cited by 3 | PDF Full-text (841 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Statistical copolymers of norbornene (NBE) with cyclopentene (CP) were prepared by ring-opening metathesis polymerization, employing the 1st-generation Grubbs’ catalyst, in the presence or absence of triphenylphosphine, PPh3. The reactivity ratios were estimated using the Finemann-Ross, inverted Finemann-Ross, and Kelen-Tüdos graphical methods,
[...] Read more.
Statistical copolymers of norbornene (NBE) with cyclopentene (CP) were prepared by ring-opening metathesis polymerization, employing the 1st-generation Grubbs’ catalyst, in the presence or absence of triphenylphosphine, PPh3. The reactivity ratios were estimated using the Finemann-Ross, inverted Finemann-Ross, and Kelen-Tüdos graphical methods, along with the computer program COPOINT, which evaluates the parameters of binary copolymerizations from comonomer/copolymer composition data by integrating a given copolymerization equation in its differential form. Structural parameters of the copolymers were obtained by calculating the dyad sequence fractions and the mean sequence length, which were derived using the monomer reactivity ratios. The kinetics of thermal decomposition of the copolymers along with the respective homopolymers was studied by thermogravimetric analysis within the framework of the Ozawa-Flynn-Wall and Kissinger methodologies. Finally, the effect of triphenylphosphine on the kinetics of copolymerization, the reactivity ratios, and the kinetics of thermal decomposition were examined. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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Review

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Open AccessFeature PaperReview ROMP Synthesis of Iron-Containing Organometallic Polymers
Molecules 2016, 21(2), 198; doi:10.3390/molecules21020198
Received: 28 December 2015 / Accepted: 2 February 2016 / Published: 6 February 2016
Cited by 10 | PDF Full-text (3394 KB) | HTML Full-text | XML Full-text
Abstract
The paper overviews iron-containing polymers prepared by controlled “living” ring-opening metathesis polymerization (ROMP). Developments in the design and synthesis of this class of organometallic polymers are highlighted, pinpointing methodologies and newest trends in advanced applications of hybrid materials based on polymers functionalized with
[...] Read more.
The paper overviews iron-containing polymers prepared by controlled “living” ring-opening metathesis polymerization (ROMP). Developments in the design and synthesis of this class of organometallic polymers are highlighted, pinpointing methodologies and newest trends in advanced applications of hybrid materials based on polymers functionalized with iron motifs. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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Open AccessReview NHC Backbone Configuration in Ruthenium-Catalyzed Olefin Metathesis
Molecules 2016, 21(1), 117; doi:10.3390/molecules21010117
Received: 29 November 2015 / Revised: 9 January 2016 / Accepted: 11 January 2016 / Published: 20 January 2016
Cited by 10 | PDF Full-text (5973 KB) | HTML Full-text | XML Full-text
Abstract
The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric
[...] Read more.
The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric olefin metathesis promoted by chiral catalysts bearing C2-symmetric and C1-symmetric NHCs is provided. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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